"What is the best drink with a fine cigar?" is probably the question I field most as an editor of Cigar Aficionado, especially since I do much of the spirits writing in the magazine and on the Web site. "When I reply, "Cognac, of course," -- an inadequate answer at best -- I am immediately drawn into a trap. Inevitably, the other guy prefers single-malt Scotch and wants to argue about it. Since I don't really believe it's Cognac -- at least not all of the time -- I don't answer that way.

Instead, I usually go into some long-winded discourse that is a sure cure to insomnia and never get to the main point that I would like to make most. To wit: I don't want to know what the best cigar and spirit pairing is. Then I'd have to quit sampling. Without boxing myself in, I can, however, make some generalities about which pairings work better than others (I have learned something in all these years). While it may seem axiomatic that the drink bone is connected to the smoke bone, it is my contention that some drinks offer more connective tissue.

When choosing a spirit to go with a cigar, I select in much the same way as a sommelier pairs wine with food: considering the relative flavor weights. A cigar is a pretty hefty experience. Therefore it deserves a weighty drink to go with it. The years that brown spirits spend in oak impart weighty flavors that sing harmony to most cigars. If you prefer wine, beer, vodka, gin or a cocktail with a cigar -- or that's all you have at the moment -- by all means, bottoms up. But for present purposes, I will restrict my musings to whiskey, aged rum and brandy.

Matching body weight is a convenient rule. It seems logical that a full-bodied cigar should go well with a full-bodied drink, and a mild-bodied cigar with a mild-bodied drink. After all, a big cigar will heat up the finish on a light spirit; a full-bodied spirit will overwhelm a light cigar. Two problems persist with this rule, however. First, like all generalizations, it's not always true. We've been pleasantly surprised in pairings when a big, ballsy cigar made a great partner for a light whiskey and vice versa. Second, it's a rule that's more useful for avoiding mistakes than for identifying sublime marriages.

Truly great pairings come when complex flavors within a cigar and a spirit create synergy -- that is, attributes that were not evident come to the forefront. A dull cigar suddenly smacks of cocoa; whiskey tastes of orange peel. Both cigar and spirit develop a nuttiness where it previously hadn't been. Predicting or pinpointing the causes behind such good fortune is harder than simply matching body weights. A spicy, salty cigar might soar when paired with a sweeter spirit because the tastes complement and create overtones of toast or nuts. But other pairings work because like flavors meet: a woody cigar with a smoky Scotch, for instance. Then again, chocolate and leathery-sweet cigars match well with sweet Bourbons and rums. Furthermore, a great spirit can tame a slightly savage cigar as when acid turns to flowers in the company of grand old Cognac.

So each of the classic cigar-pairing spirits -- rum, Cognac, Scotch and Bourbon -- has its own grounds on which it might claim drinking hegemony. This is how I'd argue each one's case:

Rum

Geography provides rum's claim to perfect partnership with cigars. The raw materials for each product -- sugar cane and tobacco -- grow in similar climates, sometimes very close to each other. If you apply to spirits and cigars the concept of regional affinity that is so often used in pairing wine and food -- that is, you expect local produce to match well with local wines -- rum with a smoke is a natural marriage.

It's hard to argue that the enjoyment of both won't be enhanced when lounging in a tropical setting. Easy climate and laid-back culture meld to create the mood that brings one to a smoke and a drink in the first place. It is similarly difficult to deny that Cuba, a place that grows both cigar tobacco and sugar cane, once made the best cigars and rum in the world. And they went together quite nicely, thank you.

Even if you don't buy the idea that a particular environment can imply an organic synergy on all that grows there, a certain logic applies to the proximity of production and its effect on rum and cigars. Traditionally, Caribbean cigarmakers have been rum drinkers because that was the spirit made where they worked. Similarly, rum men smoked cigars due to their availability and place in the culture. They enjoyed the pleasures simultaneously and, consciously or not, created their respective concoctions to go with the other. You don't smoke cigars and create a spirit that is at odds with it. You don't drink rum and roll cigars to be smoked with white wine.

Consider also what rum is made from: sugar. Sweetness goes with smoke like chocolate goes with salty nuts. The competing tastes complement each other perfectly, the first taking the tart edge off the other, while the second reins in its partner's tendency to cloy. Rums needn't be especially old to confer that inherent sweetness because the spirit matures quickly when aged, as it so often is, in hot climates. Rum is already relatively cheap because it's generally produced where costs are low. This is a cigar-friendly drink with a lot of bang for the buck.

That said, flaws exist in the argument. Not all rum is made in the Caribbean, or in the tropics for that matter. While cane is certainly tropical, it is often shipped to remote locations in the form of molasses to be fermented and distilled in industrial environments, losing any hope of retaining local flavor. And while some rums soar to great heights, the lack of any official quality standards results in products that span a range from rot gut to the sublime. Rum can be distilled at the hottest proofs or can be artificially flavored. It doesn't have to be aged and, when it is, its stated age can merely be an average instead of the age of the youngest spirit in the blend as with other brown goods. Ingredients vary -- pure cane or molasses -- and rum can be pot-stilled, column-stilled or a blend of the two. Your enjoyment of a particular quaff will depend greatly on which of these qualities you prefer.

Furthermore, today's cigarmaker isn't as apt to limit his drinking to just rum. As the world gets smaller, other spirits are available in remote regions. We know cigarmakers who lay in supplies of fine Scotches, Cognacs and wine at their backwater farms. So maybe he's not rolling for rum, as it were. Likewise, tobacco isn't all grown or rolled in the Caribbean or Central America. The Connecticut River Valley in the dead of winter is about as un-tropical as you can get.

If you were to blindfold me at the bar with a cigar in mouth and ask me to choose a house-call spirit, it wouldn't be rum. Rum at its worst -- hot, raw and full of fusel oil -- is the cigar's worst enemy. It will find any rough spot in the smoke and exacerbate it until you wish you weren't having either. But put me on a palm-filled beach at sunset with a great cigar and any of the following rums and I am in paradise.

BACARDI * A lush mixture of vanilla, caramel and licorice with an elegant complexity and a delicate finish. Especially good with full-bodied cigars. Sweetness may overpower lighter fare.

ANIVERSARIO PAMPERO Extreme finesse tempers an explosion of sugar (honey) and spice (ginger, cloves, cinnamon and tea). Seeks out leather and chocolate in a cigar and endeavors to accentuate them.

APPLETON ESTATE DISTILLED 21-YEAR-OLD A nose full of vanilla, oak and butterscotch followed by sweet wood, walnuts and licorice. Sweetness fills rough spots in a cigar and coaxes out wood.

MONTECRISTO RUM 12 YEAR AGED Molasses sweet with maple sugar and vanilla and a ginger finish. Developed by the cigar retailers the Frey Boys, it pairs well with a wide variety of smokes.

MOUNT GAY EXTRA OLD Vanilla, citrus and ginger in a straightforward medium-bodied rum. Pairs well with like-bodied cigars and finds surprising synergies.

RHUM BARBANCOURT ESTATE RESERVE A profusion of coconut, cream and honeysuckle, but contains a slight fusel oil taste as a by-product of the pot still. The right cigar turns it to flowers and spice.

SANTA TERESA 1796 RON ANTIGUO DE SOLERA A complex medium-bodied rum that pairs well with cigars from mild to full body. Brings spice, wood and leather to the party. Takes on cream.

RON ZACAPA CENTENARIO Intense nose of sugar and ginger, followed by a litany of tropical fruits -- lemon, lime, passion fruit, etc. Finish is short, but sweet and strong.

Cognac

Tradition taps Cognac as the preeminent cigar match. As an addendum to a grand dinner party, the pair is not only an institution, but a clichè of novels, plays and movies. The guests arise ceremoniously from an elegant table, the ladies head for tea in the parlor, the gentlemen for a brandy and a smoke in the drawing room. The plot thickens. And, as it is with so many clichès, this one got to be that way because it is so true or at least can be.

Certainly, timing has much to do with how the pairing evolved. Cognac is a postprandial drink; a cigar after dinner is a necessity. By default, we enjoy the two at the same time. Any other time of the day, the matchup doesn't seem as obvious. You're either not drinking brandy or it's mixed in a cocktail that doesn't suggest a smoking allegiance. Cognac may not be the universal cigar partner, but when the two are introduced correctly it is sublime.

Cognac is the distilled product of fermented grapes (mainly ugni blanc) of a region surrounding the town of Cognac in the district of Charente on the central west coast of France. The wine's charm owes much to the high chalk content in the soil. The distinction Grande Champagne when applied to Cognac reflects the literal meaning of champagne (field) and has nothing to do with the sparkling wine that comes from the Champagne province hundreds of miles away in the northeast except that it comes from a similarly chalky region. The Cognac region is divided into crus that form six roughly concentric circles starting at the center with Grande Champagne, and working out through Petite Champagne to Bois Ordinaires. The closer to the center of the circle, the more prized the wine. The designation "Fine Champagne" indicates brandy made exclusively from the grapes of the Grande and Petite Champagne regions, at least 50 percent of which have to come from Grande Champagne. "Grande Fine" or "Grande Champagne" on the bottle means every grape comes from Grande Champagne. That is not to say that Cognacs without that designation are necessarily inferior. It is a blender's art, and the use of some wines from the region's extremities can serve to round out some of the oldest and greatest brandies.

Oddly, the wine of the region is of poor quality until it is made into brandy, when it becomes royalty. It is the double distillation in pot stills, along with aging in the fine Limousin oak barrels of the region, that gives it its pedigree. First distilled, some 400 years ago, Cognac immediately distinguished itself as superior to most other brandy wines. Then about 200 years later, about the same time spirits makers the world over were discovering the advantages of aging, Cognac makers began using wood from nearby forests to make barrels to store their brandy. The local oak with its loose grain proved so excellent for aging brandy, imparting its signature floral character.

Cognac is most commonly divided into three categories of age: VS, VSOP and XO. While VS stands for "very superior" or "very special," it isn't
particularly. The designation merely indicates at least two years of aging -- a duration that yields a brandy suitable for mixing in cocktails. For the purpose of cigar pairing, however, these brandies usually fall flat, bringing little to the party. The VSOP designation means "very special old pale" and indicates aging of at least four years; it is at this level that the cigar pairing becomes plausible. In particular, mild- and medium-bodied cigars seem to go well with VSOPs. It isn't until the XO ("extra old") level, when a six-and-a-half-year minimum age is required, that the cigar begins to sing its best harmony to Cognac. The age requirement at that level is usually not a very accurate reflection of the high quality of the spirit, as brandies of 30 years, and sometimes as many as 50 can be part of the blend. Fuller-bodied cigars enjoy the charms of such fine Cognac.

A number of Cognacs have been expressly created in recent years for pairing with cigars, such as A. Fussigny Cigare and the Davidoff Cognacs. Among their many attributes is that they provide a fine cigar accompaniment at a price that can be easier on the wallet than the stratospheric prices of many XOs.

While Cognac is the best known, traditional brandy for cigars, it would be a shame to ignore Armagnac, its French cousin to the south, and the burgeoning brandies of California. Armagnac enjoys a longer tradition than Cognac, but has suffered from marketing failures in America. Its chief differences come from the preponderance of sand in the soil and its method of distillation. A single run is made in a special still that allows it to retain more of the raw qualities of the grape. The best California brandy makers are quickly catching up to their French counterparts by adhering to the traditional methods of grape selection, distillation and Limousin oak aging.

When you find yourself partaking in the brandy-and-cigar tradition, note that one part of the clichè may be erroneous. Most connoisseurs do not use the huge, ball-shaped brandy snifter, but prefer a smaller tulip-shaped glass that concentrates the aroma rather than asphyxiating you with it. The former shape is probably a holdover from the days when room temperatures were so cold it was necessary to warm the drink in your hand. Whatever glass you have, try some of the following brandies with your favorite cigar.

COGNACS

MARTELL XO Supreme balance in a Cognac that combines flowers, anise, bread dough, walnuts and candy. Pairs best with mild to medium cigars, but won't wither with a full.